The setup
TrainLoop is a platform that fine-tunes large language models into specialized AI systems using reinforcement learning. Jackson Stokes is the CEO.
During his time at YC, Jackson realized that he and his co-founder weren't the right fit to build a company together. They had different strengths and were right for different things. At the time, it felt like the end of the world. He had tied up so much in the concept of the company being the thing that needs to succeed.
What David and Michael did
David Lieb and Michael Seibel are Group Partners at YC. The YC partners at the earliest stages spend roughly half their time advising on the company and half just being supportive of the founder's personal journey. They know the company isn't going to be firing on all cylinders that early. What matters more is making sure the founder stays in it for the long run.
- Both David and Michael were generous with their time after the co-founder split. They sat with Jackson and helped him see that the real asset wasn't the company itself. It was his own growth as a founder.
- They put the experience in context of a 20-year entrepreneurial career, not just the last six months. Their framing was simple: did you really expect it to go perfectly the first time? Did you expect there wouldn't be growth or setbacks along the way?
- They helped Jackson come out of that chapter in high spirits, with new information and the energy to start the next one.
The result
Jackson went on to co-found TrainLoop with Mason Pierce and got into YC's W25 batch.
"The value isn't in the company itself. It's that we as founders are growing. Even if this one doesn't work out, you can turn around and still be in high spirits to start the next one with new information."
— Jackson Stokes, CEO & Co-Founder, TrainLoop
The takeaway
Most of what David and Michael did was just being present and honest. They had the experience of watching hundreds of founders go through the same thing, and they used that context to remind Jackson that a 20-year career doesn't hinge on the first six months. That kind of perspective is hard to find when everything feels like it matters more than it does.